This painting depicts one of the hunting scenes from the medieval Ballad of Chevy Chase wherein the Earl of Northumberland led his hunting party into Scotland's Cheviot Hills to hunt a chase of land, the term Chevy Chase is derived from this ballad. Landseer based his preparatory sketch and the final painting of The Hunting of Chevy Chase on the deer hunt described in the first nine stanzas of the above-mentioned poem. Some sketches similar in size found in Landseer's studio indicated that he might have intended to paint another painting based on the closing stanzas of the poem.

Landseer was very meticulous in his work as an artist and before the final painting completed a preparatory sketch in oil of the final painting which he did on a panel of which the dimensions was 45,7 x 61cm. The sketch in oil was sold in 1974 by Sotheby’s in London. In his earlier works with the motif of the stag and hunting dogs, Landsdeer laid the foundational motif for the Hunting of Chevy Chase. The painting The Hunting of Chevy Chase 143 x 171cm is widely regarded as one of Landseer's most important paintings and can be viewed in the Birmingham Museums and Art Gallery, which acquired it during 1951. The painting depicts a very lively scene in which the focus is on the hunt and not on the battle described in the ancient ballad. In the foreground, we find the lively group of contorted animals consisting of dogs, the stag, and the female hind.

Landseer was greatly inspired by the Flemish hunting scenes painted by Rubens and Frans Snyders. The rearing horse with a rider is borrowed from Rubens's Wolf and Fox Hunt and the stag and leaping hind is borrowed from Snyders Staghunt. Before painting The Hunting of Chevy Chase Landseer sketched Rubens's Wolf and Fox Hunt in preparation. With his painting, Landseer captured the spirit of the Rubens painting which greatly influenced him. The brushwork and lighting effects which are both transparent and sparkling bears testimony of his fondness of the hunting scenes painted by Rubens. With the painting, Landseer also captures the Scottish landscape and its romantic imagery as portrayed in the poetry of Sir Walter Scott who also influenced Landseer.